Benzoyl Peroxide → HCID 20026476, compound

HRID 1723034Notes

Reaction equation

HRID 1723034 reaction equation
C1C(=O)N([Br:8])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[C:39]([CH3:40])=[CH:38][N:37]=[C:36]([CH3:41])[N:35]=2)=[CH:30][CH:29]=1.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Br:8][CH2:40][C:39]1[C:34]([C:31]2[CH:30]=[CH:29][C:28]([Cl:27])=[CH:33][CH:32]=2)=[N:35][C:36]([CH3:41])=[N:37][CH:38]=1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 11439SuccinimideHCID 67184N-bromobutanimide2×HCID 20026479HCID 20026479, compound

Product 1

HCID 20026476HCID 20026476, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2.26 g (12.7 mmol) of NBS and 3 mg of dibenzoyl peroxide were added to a solution of 2.73 g (12.5 mmol) of 4-(4-chlorophenyl)-2,5-dimethylpyrimidine in 48 ml of CCl4, and the mixture was refluxed for 5 minutes with stirring and irradiation (cf. Example 25). The NBS had then been converted into succinimide. This was filtered off at room temperature through a filtration aid and washed with CCl4, and the filtrate was evaporated in vacuo. The residue was dissolved in about 60 ml of diisopropyl ether/n-pentane 1:1, the slightly turbid solution was clarified using kieselguhr and again filtered under suction, and the clear filtrate was evaporated in an oil-pump vacuum to constant weight. According to the 1H NMR spectrum, the residue (3.4 g) comprised 69.5% purity 5-bromomethyl-4-(4-chlorophenyl)-2-methylpyrimidine (=63.5% yield). This bromomethyl compound was used in this form for the reaction with 1-(4-hydroxyphenyl)piperazine (cf. Example 23, No. 5.19).

Workup

  1. temperaturethe mixture was refluxed for 5 minutes
  2. customirradiation (cf. Example 25)
  3. filtrationThis was filtered off at room temperature through a filtration aid
  4. washwashed with CCl4
  5. customthe filtrate was evaporated in vacuo
  6. dissolutionThe residue was dissolved in about 60 ml of diisopropyl ether/n-pentane 1:1
  7. filtrationagain filtered under suction
  8. customthe clear filtrate was evaporated in an oil-pump vacuum to constant weight

Sources & evidence

ORD record
ord-b8910c0f652647da845898062fd813e1
Source dataset
uspto-grants-1989_08
Patent number
US04859670

Reaction notes

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